NPASS Compound

Natural Product: NPC603867

Natural Product ID	NPC603867
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BYSLEZZCJZXNQG-FZHSXGHWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4528043
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 92 96 0 0 0 0 0 0 0 0999 V2000 9.1532 2.1393 -0.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9910 1.4196 0.4941 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8246 2.2742 0.7570 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1512 0.1869 0.8023 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3864 -0.8458 1.4272 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9434 -0.7807 1.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0774 -0.6733 0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2162 -1.7629 -0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2093 0.3126 0.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 0.3142 -0.8748 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9317 0.2020 -0.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0347 0.2499 -1.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5549 0.4167 -2.9765 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3327 0.1457 -1.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2646 0.2359 -2.6732 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3124 -0.9650 -3.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7020 -2.0987 -3.4009 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0482 -3.1235 -4.4959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2809 -2.5965 -2.4299 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -0.0211 -0.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0203 -0.0741 0.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3984 0.0384 0.6213 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2035 -0.0220 1.7266 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5440 -0.2506 2.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2129 -0.3022 3.1635 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9721 -0.3681 2.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 -0.4876 3.5188 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0161 -0.9304 3.4054 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9698 -2.1245 2.4500 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6135 -1.7011 1.0637 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7687 -1.2636 0.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4893 -1.6000 -1.2542 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0757 -1.8660 0.6387 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8668 0.1019 0.2951 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0740 0.5428 1.3487 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7001 1.9828 1.2310 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9345 2.7892 1.2131 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2036 3.5469 0.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2837 3.5976 -0.9782 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4450 4.3529 0.1592 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6819 0.1640 2.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6693 0.6765 3.1282 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8472 -0.3664 1.1723 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2074 -0.1324 -0.0442 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0605 1.5919 0.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1568 3.1717 0.1441 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0298 2.0341 -1.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1874 2.2506 -0.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1459 3.3556 0.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2072 2.0168 1.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2268 -0.1745 0.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9346 -1.2378 2.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5269 -1.7903 0.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6697 -0.0235 2.4885 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6727 -1.8113 2.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9045 -2.5606 -0.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2443 -2.2698 -0.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5624 -1.3821 -1.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1047 1.1102 1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7243 -0.5132 -1.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5504 1.2489 -1.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2040 1.1769 -3.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0238 1.1289 -3.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 0.3787 -2.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0246 -0.8889 -4.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0049 -2.8468 -4.9339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1914 -3.1528 -5.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1020 -4.1300 -4.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2886 -3.7460 -2.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0444 -2.4107 -1.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3428 -2.3643 -2.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5536 -0.8546 2.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1861 -0.3156 4.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4689 -1.1669 4.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8468 -2.7692 2.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1027 -2.7450 2.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9633 -2.4480 0.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3000 -2.2690 -1.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4950 -2.0794 -1.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5188 -0.7092 -1.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2671 -1.5836 1.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0828 -2.9642 0.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8789 -1.3470 0.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9934 2.2829 2.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1729 2.1090 0.2675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6311 2.7583 2.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1375 2.5973 -1.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6656 4.3246 -1.7470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 4.0286 -0.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1679 5.4013 0.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1810 3.9295 0.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8716 4.3249 -0.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 2 3 17 18 1 0 17 19 1 0 14 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 21 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 34 35 1 0 35 36 1 1 36 37 1 0 37 38 2 3 38 39 1 0 38 40 1 0 35 41 1 0 41 42 2 0 35 43 1 0 43 44 1 6 22 11 1 0 43 26 1 0 44 20 1 0 41 28 1 0 43 30 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 8 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 13 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 18 66 1 0 18 67 1 0 18 68 1 0 19 69 1 0 19 70 1 0 19 71 1 0 23 72 1 0 27 73 1 0 28 74 1 1 29 75 1 0 29 76 1 0 30 77 1 6 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 36 84 1 0 36 85 1 0 37 86 1 0 39 87 1 0 39 88 1 0 39 89 1 0 40 90 1 0 40 91 1 0 40 92 1 0 M END

Standard InCHIKey	BYSLEZZCJZXNQG-FZHSXGHWSA-N
Standard InCHI	InChI=1S/C38H48O6/c1-21(2)11-10-12-24(7)14-16-26-31(39)27(15-13-22(3)4)34-30(32(26)40)33(41)28-19-25-20-29-36(8,9)44-37(35(25)42,18-17-23(5)6)38(28,29)43-34/h11,13-14,17,19,25,29,39-40H,10,12,15-16,18,20H2,1-9H3/b24-14+/t25-,29+,37+,38-/m1/s1
SMILES	CC(C)=CCC/C(C)=C/Cc1c(O)c(CC=C(C)C)c2c(c1O)C(=O)C1=C[C@@H]3C[C@H]4C(C)(C)O[C@@](CC=C(C)C)(C3=O)[C@@]14O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.35	Volume:	649.398 ? Van der Waals volume.
Dense:	0.924	LogP:	8.632 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.244 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.029 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	28.0
TPSA:	93.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.278	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.387	Fsp³:	0.526
MCE-18:	164.069 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.103 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.675 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.9 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.426	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.954	MDCK Permeability:	-4.67
Pgp-inhibitor:	1.0	Pgp-substrate:	0.011
PAMPA:	0.08 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.941
Plasma Protein Binding (PPB):	96.15%	Volume Distribution (VD):	0.274
Fu:	4.193% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.961	BCRP inhibitor:	0.628
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.953	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.664

Half-life (T1/2):

1.02

ADMET: Toxicity

hERG Blockers:	0.112	hERG Blockers (10um):	0.665
Human Hepatotoxicity (H-HT):	0.96	Drug-induced Liver Injury (DILI):	0.871
AMES Toxicity:	0.492	Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.9	Skin Sensitization:	0.996
Carcinogencity:	0.396	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.505	Ototoxicity:	0.943
Hematotoxicity:	0.887	Drug-induced Nephrotoxicity:	0.934
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.416
A549 Cytotoxicity:	0.685	Hek293 Cytotoxicity:	0.657
BCF:	1.964 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.769 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.126 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.125 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1820	Cell line	NCI-H1650	Homo sapiens	IC50	=	1100.0	nM	PMID[30830783]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC603867 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	13727
0.1-0.2	34451
0.2-0.3	1460
0.3-0.4	169
0.4-0.5	14
0.5-0.6	26
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC286422
0.8333	Intermediate Similarity	NPC611384
0.7403	Intermediate Similarity	NPC94796
0.7403	Intermediate Similarity	NPC611777
0.6882	Remote Similarity	NPC189689
0.6517	Remote Similarity	NPC476255
0.6512	Remote Similarity	NPC131578
0.6512	Remote Similarity	NPC611483
0.6465	Remote Similarity	NPC162248
0.6386	Remote Similarity	NPC607281
0.6353	Remote Similarity	NPC482614
0.5978	Remote Similarity	NPC223413
0.5977	Remote Similarity	NPC608101
0.5882	Remote Similarity	NPC476056
0.5882	Remote Similarity	NPC488723
0.5783	Remote Similarity	NPC475107
0.5783	Remote Similarity	NPC43490
0.5783	Remote Similarity	NPC605777
0.5747	Remote Similarity	NPC488724
0.5657	Remote Similarity	NPC158329
0.5657	Remote Similarity	NPC55422
0.5657	Remote Similarity	NPC75141
0.5618	Remote Similarity	NPC488712
0.5618	Remote Similarity	NPC475080
0.5618	Remote Similarity	NPC488719
0.5588	Remote Similarity	NPC476216
0.5435	Remote Similarity	NPC488714
0.5435	Remote Similarity	NPC488713
0.5426	Remote Similarity	NPC476162
0.5408	Remote Similarity	NPC40089
0.5408	Remote Similarity	NPC47634
0.54	Remote Similarity	NPC476311
0.5393	Remote Similarity	NPC479154
0.5333	Remote Similarity	NPC193222
0.5111	Remote Similarity	NPC62444
0.5111	Remote Similarity	NPC482613
0.5094	Remote Similarity	NPC476146

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC603867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4608
0.1-0.2	4520
0.2-0.3	22
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data